Efficient Synthesis of Benzothiazolone Derivatives by a Domino Reaction of Disulfide and COS under Mild Conditions was written by Zhou, Bohao;Hong, Hailong;Wang, Hongcai;Zhang, Tianmiao;Han, Limin;Zhu, Ning. And the article was included in European Journal of Organic Chemistry in 2018.Electric Literature of C7H4ClNOS This article mentions the following:
Carbonyl sulfide (COS), whose mol. structure is similar to CO2 and CS2, could be used as a better alternative carbonyl reagent due to its high chem. activity. However, the unfriendly byproduct H2S would be generated when COS is used as a carbonyl reagent in the carbonylation reaction. In this report, the odorless and stable disulfide was used to replace the traditional foul smelling and unstable o-aminobenzenethiol to react with COS for preparing benzothiazolone derivatives in excellent yield, in which coupling reaction of H2S generation and S-S bond cleavage was firstly designed. Notably, the C=O of COS was converted into benzothiazolone derivatives by carbonylation reaction and the sulfur of COS was transformed into sulfur and sulfide after cleaving the S-S bond by a domino reaction of disulfide and COS under mild conditions. This efficient synthetic methodol. provided a promising process for the utilization of COS. In the experiment, the researchers used many compounds, for example, 6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3Electric Literature of C7H4ClNOS).
6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 °C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Electric Literature of C7H4ClNOS
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica